2-Bromo-1-(4-hydroxyphenyl)ethanone → 4-[6-(Cyclopropylmethoxy)imidazo[1,2-a]pyridin-2-yl]phenol

HRID 1026313Notes

Reaction equation

[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([NH2:12])=[N:10][CH:11]=2)[CH2:3][CH2:2]1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)=O>C(O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=4)[N:12]=3)[CH:11]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-(cyclopropylmethoxy)pyridin-2-amine (328 mg), 2-bromo-1-(4-hydroxyphenyl)ethanone (430 mg) and ethanol (10 mL) was stirred at 80° C. for 4 hr. The reaction mixture was allowed to cool to room temperature, and the resulting crystals were collected by filtration. The obtained crystals were dissolved in saturated aqueous sodium hydrogen carbonate solution and THF, and the solution was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a brown solid (561 mg).

Workup

temperatureto cool to room temperature
filtrationthe resulting crystals were collected by filtration
dissolutionThe obtained crystals were dissolved in saturated aqueous sodium hydrogen carbonate solution
extractionTHF, and the solution was extracted twice with ethyl acetate
washThe combined organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-36e985b3248a49219b2ac22179955b48
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729102B2

Reaction notes

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